CN109574959A - A kind of thiamines 1,4- naphthoquinone compound and preparation method thereof - Google Patents
A kind of thiamines 1,4- naphthoquinone compound and preparation method thereof Download PDFInfo
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- CN109574959A CN109574959A CN201910040030.8A CN201910040030A CN109574959A CN 109574959 A CN109574959 A CN 109574959A CN 201910040030 A CN201910040030 A CN 201910040030A CN 109574959 A CN109574959 A CN 109574959A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
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Abstract
The present invention uses naphthoquinones, amine, mercaptan for raw material, proposes a kind of preparation method of thiamines 1,4-naphthoquinone class compound.The synthesising method reacting condition is mild, under copper catalytic condition, oxygen is oxidant, single step reaction can synthesize a variety of thiaminesization 1,4- naphthoquinone compound, provides a kind of simple and effective, and raw material and catalyst are cheap and easy to get, the synthetic method of the highly effective of wide adaptability has good application value and market prospects.
Description
Technical field
The present invention relates to the field of chemical synthesis, and in particular to a kind of preparation method of thiamines 1,4-naphthoquinone compound.
Background technique
Thiamines 1,4-naphthoquinone compound is a kind of important organic compound, due to its unique bioactivity and antibacterial
Performance and be widely used in the fields such as Synthetic Organic Chemistry, biochemistry and pharmaceutical chemistry.Generally, thiamines 1,4-naphthoquinone
Compound can be synthesized (such as: RSC Adv., 2014,4,12441-12447. by the nucleophilic substitution of naphthoquinones halide
Acc Chem Res, 2015,48,1756-1766.), and the reaction is starting material using halogenated naphthoquinones, in two steps with sulphur
Alkohol and amine is reacted.Such reaction needs synthesizing halogen naphthoquinones substrate；Catalyst system is complicated simultaneously, can not accomplish that a step is anti-
It answers；Reaction efficiency is not high, and substrate applicability is bad.In addition, although the thiaminesization of 1,4-naphthoquinone can be anti-by Michael's addition
It should realize (Heteroat Chem, 2005,16,205-211.).But it cannot achieve single step reaction, and reactive adaptation
Property is bad.Announced in the present invention catalytic amount cuprous iodide effect under using 1,4- naphthoquinones, mercaptan, secondary amine as one step of raw material
The method of naphthoquinones thiamines class compound is efficiently synthesized temporarily without pertinent literature and patent report.
Summary of the invention
The invention proposes a kind of preparation method of thiamines 1,4-naphthoquinone compound, provide it is a kind of efficiently, wide adaptability,
The synthetic method of catalytic amount copper catalysis.The synthesising method reacting condition is mild, under copper catalytic condition, reacts in carrier of oxygen, letter
Just efficiently, raw material and catalyst are cheap and easy to get, are a kind of synthetic methods of highly effective.
It realizes the technical scheme is that a kind of thiamines 1,4-naphthoquinone compound, structural formula are as follows:
Wherein, R1For methyl, ethyl, chlorine, fluorine etc.；R2For pyridine, morpholine, pyrroles, thiomorpholine etc..
The preparation method of the thiamines 1,4-naphthoquinone compound, steps are as follows: by catalyst, 1,4-naphthoquinone, mercaptan,
Amine and solvent are added in reaction tube, then drain air, are passed through the oxygen of an atmospheric pressure, under 100 DEG C of heating, stirring condition
Reaction, obtains 1,4-naphthoquinone sulphur aminate.
The structural formula of the 1,4- naphthoquinones is as follows:
。
The structural formula of the mercaptan is as follows:
,
Wherein, R1For methyl, ethyl, chlorine, fluorine.
The structural formula of the amine is as follows:
Wherein, R1For pyridine, morpholine, pyrroles, thiomorpholine etc..
The solvent is N,N-dimethylformamide (DMF)；Catalyst is cuprous iodide；Being passed through oxygen is oxygen ball.
The 1,4- naphthoquinones, mercaptan, amine and catalyst molar ratio be 1:1:3.5:0.2.
The reaction temperature is 100 DEG C, and the reaction time is 10 h.
The reaction formula of preparation method of the present invention is as follows:
The beneficial effects of the present invention are: the present invention provides the preparation method that an a kind of step realizes 1,4-naphthoquinone thiamines, it is described
Method does not need the metallic addition of addition equivalent, carries out in oxygen gas, can efficiently synthesize thiamines 1,4-naphthoquinone compound.
It is easy to operate and safe involved in this method, have the advantages that reaction condition is simple, good economy performance, highly effective.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical solution of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Those of ordinary skill in the art's every other embodiment obtained under that premise of not paying creative labor, belongs to this hair
The range of bright protection.
Embodiment 1
The preparation method of thiamines 1,4-naphthoquinone compound, steps are as follows:
Cuprous iodide (20 mol%) is added in 25 mL reaction tubes, 0.5 mmol of 1,4-naphthoquinone, 2 mL of solvent DMF, to first
0.5 mmol of base benzenethiol, 1.75 mmol of nafoxidine are stirred in oxygen atmosphere, and control reaction temperature is 100 DEG C, reaction
After 10 hours, the isolated final product of silica gel column chromatography, by 1,4-naphthoquinone mole be 100 % in terms of, the yield of final product is
80 %。
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.10 (dd, J = 7.7, 1.3 Hz, 1H), 7.93
(dd, J = 7.7, 1.3 Hz, 1H), 7.69 (td, J = 7.5, 1.4 Hz, 1H), 7.60 (td, J = 7.5,
1.3 Hz, 1H), 7.05 (q, J = 8.3 Hz, 5H), 3.94 – 3.85 (m, 4H), 2.28 (s, 3H),
1.85 – 1.77 (m, 4H). 13C NMR (101 MHz, Chloroform-d) δ 184.38, 180.28, 155.60,
135.05, 134.77, 134.08, 133.46, 131.95, 131.89, 129.58, 126.38, 126.23,
125.89, 105.65, 53.81, 25.50, 20.93。
Embodiment 2
The preparation method of thiamines 1,4-naphthoquinone compound, steps are as follows:
Cuprous iodide (20 mol%) is added in 25 mL reaction tubes, 0.5 mmol of 1,4-naphthoquinone, 2 mL of solvent DMF, to second
0.5 mmol of base benzenethiol, 1.75 mmol of nafoxidine, oxygen atmosphere stirring, control reaction temperature are 100 DEG C, reaction 10
After hour, the isolated final product of silica gel column chromatography, be 100 % by 1,4-naphthoquinone mole in terms of, the yield of final product is 65
%。
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.11 (dd, J = 7.7, 1.3 Hz, 1H), 7.94
(dd, J = 7.6, 1.3 Hz, 1H), 7.70 (td, J = 7.5, 1.4 Hz, 1H), 7.61 (td, J = 7.5,
1.3 Hz, 1H), 7.13 – 7.04 (m, 4H), 3.97 – 3.85 (m, 4H), 2.58 (q, J = 7.6 Hz,
2H), 1.87 – 1.75 (m, 4H), 1.20 (t, J = 7.6 Hz, 3H). 13C NMR (101 MHz,
Chloroform-d) δ 184.43, 180.30, 155.63, 141.19, 135.23, 134.10, 133.46,
131.94, 131.91, 128.40, 126.41, 126.23, 125.90, 105.59, 53.83, 28.32, 25.51,
15.57。
Embodiment 3
The preparation method of thiamines 1,4-naphthoquinone compound, steps are as follows:
Cuprous iodide (20 mol%) is added in 25 mL reaction tubes, 0.5 mmol of 1,4-naphthoquinone, 2 mL, 2- chlorine of solvent DMF
0.5 mmol of benzenethiol, 1.75 mmol of nafoxidine are stirred in oxygen atmosphere, and control reaction temperature is 100 DEG C, reaction 10
After hour, the isolated final product of silica gel column chromatography, be 100 % by 1,4-naphthoquinone mole in terms of, the yield of final product is 65
%。
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.09 (dd, J = 7.8, 1.2 Hz, 1H), 7.93
(dd, J = 7.6, 1.3 Hz, 1H), 7.69 (td, J = 7.6, 1.4 Hz, 1H), 7.61 (td, J = 7.6,
1.4 Hz, 1H), 7.30 (dd, J = 7.8, 1.4 Hz, 1H), 7.09 (td, J = 7.6, 1.5 Hz, 1H),
7.01 (td, J = 7.6, 1.7 Hz, 1H), 6.93 (dd, J = 7.8, 1.6 Hz, 1H), 3.96 – 3.87
(m, 4H), 1.90 – 1.79 (m, 4H). 13C NMR (101 MHz, Chloroform-d) δ 184.37,
179.93, 157.12, 138.02, 134.28, 133.43, 132.02, 132.00, 130.59, 129.46,
127.08, 126.88, 126.46, 126.05, 125.58, 102.09, 54.07, 25.48。
Embodiment 4
The preparation method of thiamines 1,4-naphthoquinone compound, steps are as follows:
Cuprous iodide (20 mol%) is added in 25 mL reaction tubes, 0.5 mmol of 1,4-naphthoquinone, 2 mL, 4- fluorine of solvent DMF
0.5 mmol of benzenethiol, 1.75 mmol of nafoxidine are stirred in oxygen atmosphere, and control reaction temperature is 100 DEG C, reaction 10
After hour, the isolated final product of silica gel column chromatography, be 100 % by 1,4-naphthoquinone mole in terms of, the yield of final product is 70
%。
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.07 (dd, J = 7.6, 1.3 Hz, 1H), 7.91
(dd, J = 7.6, 1.3 Hz, 1H), 7.68 (td, J = 7.5, 1.4 Hz, 1H), 7.59 (td, J = 7.5,
1.3 Hz, 1H), 7.16 – 7.10 (m, 2H), 6.91 (t, J = 8.7 Hz, 2H), 3.94 – 3.84 (m,
4H), 1.86 – 1.80 (m, 4H). 13C NMR (101 MHz, Chloroform-d) δ 184.33, 180.21,
162.03, 159.60, 156.04, 134.20, 133.86 (d, J = 3.2 Hz), 133.35, 131.95 (d, J
= 12.8 Hz), 127.89 (d, J = 7.6 Hz), 126.38, 125.97, 115.91 (d, J = 22.0 Hz),
105.03, 54.03, 25.50。
Embodiment 5
The preparation method of thiamines 1,4-naphthoquinone compound, steps are as follows:
Cuprous iodide (20 mol%) is added in 25 mL reaction tubes, 0.5 mmol of 1,4-naphthoquinone, 2 mL, 4- first of solvent DMF
0.5 mmol of base benzenethiol, 1.75 mmol of pyridine are stirred in oxygen atmosphere, and control reaction temperature is 100 DEG C, and reaction 10 is small
Shi Hou, the isolated final product of silica gel column chromatography, be 100 % by 1,4-naphthoquinone mole in terms of, the yield of final product is 75 %.
Concrete outcome is as follows:
1H NMR (400 MHz, Chloroform-d) δ 8.09 – 7.97 (m, 2H), 7.70 – 7.61 (m,
2H), 7.19 – 7.12 (m, 2H), 7.03 (d, J = 8.0 Hz, 2H), 3.40 (t, J = 5.4 Hz, 2H),
2.29 (s, 3H), 1.70 (m, J = 5.7 Hz, 4H), 1.61 (q, J = 6.6, 6.2 Hz, 4H). 13C NMR
(101 MHz, Chloroform-d) δ 182.37, 181.69, 155.01, 135.92, 133.78, 133.19,
132.72 (d, J = 15.6 Hz), 132.24, 129.63, 127.93, 126.63, 126.44, 120.00,
53.38, 26.87, 24.10, 21.06。
Embodiment 6
Amine is morpholine, and with embodiment 1, concrete outcome is as follows for other test methods and condition:
1H NMR (400 MHz, Chloroform-d) δ 8.10 – 7.97 (m, 2H), 7.67 (dt, J = 5.9,
2.3 Hz, 2H), 7.16 (d, J = 7.9 Hz, 2H), 7.05 (d, J = 7.9 Hz, 2H), 3.75 (t, J =
4.6 Hz, 4H), 3.44 (t, J = 4.5 Hz, 4H), 2.30 (s, 3H). 13C NMR (101 MHz,
Chloroform-d) δ 182.07, 181.91, 153.09, 136.49, 133.97, 132.98, 132.57,
132.19, 132.05, 129.79, 128.17, 126.75, 126.56, 122.11, 67.45, 51.81, 21.07。
Embodiment 7
Amine is thiomorpholine, and with embodiment 1, concrete outcome is as follows for other test methods and condition:
1H NMR (400 MHz, Chloroform-d) δ 8.08 – 7.99 (m, 2H), 7.71 – 7.64 (m,
2H), 7.21 – 7.16 (m, 2H), 7.06 (d, J = 8.0 Hz, 2H), 3.60 – 3.47 (m, 4H), 2.79
– 2.69 (m, 4H), 2.31 (s, 3H). 13C NMR (101 MHz, Chloroform-d) δ 182.17,
182.01, 153.56, 136.85, 133.90, 133.10, 132.49, 132.02, 131.85, 129.80,
128.70, 126.77, 126.54, 124.75, 53.66, 28.10, 21.12。
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (8)
1. a kind of thiamines 1,4-naphthoquinone compound, it is characterised in that structural formula is as follows:
,
Wherein, R1For methyl, ethyl, chlorine, fluorine etc.；R2For pyridine, morpholine, pyrroles, thiomorpholine etc..
The preparation method of thiamines 1,4-naphthoquinone compound described in 2., it is characterised in that steps are as follows: by catalyst, Isosorbide-5-Nitrae-naphthalene
Quinone, mercaptan, amine and solvent are added in reaction tube, then drain air, are passed through the oxygen of an atmospheric pressure, and 100 DEG C of heating is stirred
It is reacted under the conditions of mixing, obtains 1,4-naphthoquinone sulphur aminate.
3. the preparation method of thiamines 1,4-naphthoquinone compound according to claim 2, it is characterised in that the Isosorbide-5-Nitrae-naphthalene
The structural formula of quinone is as follows:
。
4. the preparation method of thiamines 1,4-naphthoquinone compound according to claim 2, it is characterised in that the mercaptan
Structural formula is as follows:
,
Wherein R1For methyl, ethyl, chlorine, fluorine.
5. the preparation method of thiamines 1,4-naphthoquinone compound according to claim 2, it is characterised in that: described to state solvent
For N,N-dimethylformamide (DMF)；Catalyst is cuprous iodide；Being passed through oxygen is oxygen ball.
6. the preparation method of thiamines 1,4-naphthoquinone compound according to claim 2, it is characterised in that: the Isosorbide-5-Nitrae-naphthalene
Quinone, mercaptan, amine and catalyst molar ratio be 1:1:3.5:0.2.
7. the preparation method of thiamines 1,4-naphthoquinone compound according to claim 2, it is characterised in that: the reaction
Temperature is 100 DEG C, and the reaction time is 10 h.
8. according to the preparation method of the described in any item thiamines 1,4-naphthoquinone compounds of claim 2-7, it is characterised in that institute
The structural formula for stating thiamines 1,4- naphthoquinone compound is as follows:
；
Wherein, wherein R1For methyl, ethyl, chlorine, fluorine etc.；R2For pyridine, morpholine, pyrroles, thiomorpholine etc..
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111606843A (en) * | 2020-06-17 | 2020-09-01 | 温州医科大学 | Synthetic method of 2-phenylseleno-3-amino-1, 4-naphthoquinone |
| CN111620840A (en) * | 2020-06-17 | 2020-09-04 | 温州医科大学 | Synthetic method of 2-morpholinyl-3-arylseleno naphthoquinone |
| CN113372298A (en) * | 2021-05-21 | 2021-09-10 | 温州医科大学 | Preparation method of 2-iodine-3-amino naphthoquinone compound |
| CN114213361A (en) * | 2021-12-30 | 2022-03-22 | 遵义医科大学珠海校区 | Preparation method of thiaminated 1, 4-naphthoquinone compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015172076A1 (en) * | 2014-05-09 | 2015-11-12 | Sloan-Kettering Institute For Cancer Research | Naphthaquinone methyltransferase inhibitors and uses thereof |
-
2019
- 2019-01-16 CN CN201910040030.8A patent/CN109574959A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015172076A1 (en) * | 2014-05-09 | 2015-11-12 | Sloan-Kettering Institute For Cancer Research | Naphthaquinone methyltransferase inhibitors and uses thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111606843A (en) * | 2020-06-17 | 2020-09-01 | 温州医科大学 | Synthetic method of 2-phenylseleno-3-amino-1, 4-naphthoquinone |
| CN111620840A (en) * | 2020-06-17 | 2020-09-04 | 温州医科大学 | Synthetic method of 2-morpholinyl-3-arylseleno naphthoquinone |
| CN111620840B (en) * | 2020-06-17 | 2023-06-30 | 温州医科大学 | Synthesis method of 2-morpholino-3-arylseleno naphthoquinone |
| CN113372298A (en) * | 2021-05-21 | 2021-09-10 | 温州医科大学 | Preparation method of 2-iodine-3-amino naphthoquinone compound |
| CN113372298B (en) * | 2021-05-21 | 2022-04-19 | 温州医科大学 | Preparation method of 2-iodine-3-amino naphthoquinone compound |
| CN114213361A (en) * | 2021-12-30 | 2022-03-22 | 遵义医科大学珠海校区 | Preparation method of thiaminated 1, 4-naphthoquinone compound |
| CN114213361B (en) * | 2021-12-30 | 2023-08-25 | 遵义医科大学珠海校区 | Preparation method of thiamine 1, 4-naphthoquinone compound |
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Application publication date: 20190405 |